| |||
Names | |||
---|---|---|---|
IUPAC name
Phosphorothioic trichloride
| |||
Other names
| |||
Identifiers | |||
3D model (JSmol)
|
|||
ChemSpider | |||
ECHA InfoCard | 100.021.476 | ||
EC Number |
| ||
PubChem CID
|
|||
RTECS number |
| ||
UNII | |||
UN number | 1837 | ||
CompTox Dashboard (EPA)
|
|||
| |||
| |||
Properties | |||
PSCl3 | |||
Molar mass | 169.38 g·mol−1 | ||
Appearance | Colorless liquid | ||
Density | 1.67 g/cm3 | ||
Melting point | −35 °C (−31 °F; 238 K) | ||
Boiling point | 125 °C (257 °F; 398 K) | ||
Reacts | |||
Solubility | Soluble in benzene, chloroform, CS2 and CCl4. | ||
Structure | |||
Tetrahedral at the P atom | |||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards
|
Violent hydrolysis; releasing HCl on contact with water,[2] maybe corrosive to metals and skin | ||
GHS labelling:[4] | |||
Danger | |||
H302, H314, H330 | |||
P260, P264, P270, P271, P280, P284, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P320, P321, P330, P363, P403+P233, P405, P501 | |||
Flash point | none[3] | ||
Related compounds | |||
Related compounds
|
|||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Thiophosphoryl chloride is an inorganic compound with the chemical formula PSCl3.[5] It is a colorless pungent smelling liquid that fumes in air. It is synthesized from phosphorus chloride and used to thiophosphorylate organic compounds, such as to produce insecticides.
Thiophosphoryl chloride can be generated by several reactions starting from phosphorus trichloride. The most common and practical synthesis, hence used in industrial manufacturing, is directly reacting phosphorus trichloride with excess sulfur at 180 °C.[6]
Using this method, yields can be very high after purification by distillation. Catalysts facilitate the reaction at lower temperatures, but are not usually necessary. Alternatively, it is obtained by combining phosphorus pentasulfide and phosphorus pentachloride.[7]
Thiophosphoryl chloride has tetrahedral molecular geometry and C3v molecular symmetry, with the structure S=PCl3. According to gas electron diffraction, the phosphorus–sulfur bond length is 189 pm and the phosphorus–chlorine bond length is 201 pm, while the Cl−P−Cl bond angle is 102°.[8]
PSCl3 is soluble in benzene, carbon tetrachloride, chloroform, and carbon disulfide.[5] However, it hydrolyzes rapidly in basic or hydroxylic solutions, such as alcohols and amines, to produce thiophosphates.[6] In water PSCl3 reacts, and contingent on the reaction conditions, produces either phosphoric acid, hydrogen sulfide, and hydrochloric acid or dichlorothiophosphoric acid and hydrochloric acid.[9]
PSCl3 is used to thiophosphorylate organic compounds (to add thiophosphoryl group, P=S, with three free valences at the P atom, to organic compounds).[6] This conversion is widely applicable for amines and alcohols, as well as aminoalcohols, diols, and diamines.[5] Industrially, PSCl3 is used to produce insecticides, like parathion.[9]
PSCl3 reacts with tertiary amides to generate thioamides.[5] For example:
When treated with methylmagnesium iodide, it give tetramethyldiphosphine disulfide (H3C−)2P(=S)−P(=S)(−CH3)2.[10]